Born and raised in Oshawa, Ontario, Dale DeGray began his junior hockey career in 1980 as a member of the Oshawa Generals of the Ontario Hockey League. An offensive-minded defenseman, DeGray scored 11 goals and 10 assists as an OHL rookie in 1980-81. In the spring of 1981, DeGray was drafted by the Calgary Flames in the 8th Round of the NHL Entry Draft. He was the 162nd player selected overall.

DeGray, who earned the nickname "Digger" for his solid play in the corners, repeated his 11 goal performance in 1981-82, this time chipping in 22 assists to finish second in scoring among Oshawa's defense. At the end of the season, DeGray was named Oshawa's Most Underrated Player. DeGray's last season in Oshawa was his best. In 1982-83 he scored 20 goals, the most amongst Oshawa's defensemen, and added 30 assists. He was again named Most Underrated Player for the 1982-83 season.

DeGray turned pro in 1983, joining the Calgary Flames organization. He was assigned

to the Colorado Flames, Calgary's affiliate in the Central Hockey League, for the 1983-84 season. DeGray performed well in his first professional season, scoring 16 goals and 14 assists in 67 games played.

At the end of the 1983-84 season, the Central Hockey League suspended operations. DeGray was reassigned to the Moncton Golden Flames of the American Hockey League, where he would play parts of the next three seasons. Moncton's leading defensive scorer during the 1984-85 season, DeGray made his NHL debut during the 1985-86 season, playing one game for the Calgary Flames. He split the 1986-87 season between Moncton and Calgary, scoring 6 goals and 7 assists in 27 games with Calgary.

In October of 1987, the Calgary Flames traded DeGray to the Toronto Maple Leafs for future considerations. DeGray split the 1987-88 season between the Maple Leafs and their AHL affiliate, the Newmarket Saints. He played 56 games in the NHL, accounting for 6 goals and 18 assists. DeGray was on the move again for the 1988-89 season, selected in the waiver draft by the Los Angeles Kings. He played 63 games for the Kings during the season, the longest NHL stint of his career. DeGray scored 6 goals and 22 assists for a career-high 28 points.

DeGray was reassigned to the Kings' AHL affiliate, the New Haven Nighthawks to start the 1989-90 season. On November 24, 1989 DeGray was traded along with future considerations to the Buffalo Sabres for defenseman Bob Halkidis and future considerations. DeGray was assigned to the Sabres' AHL club, the Rochester Americans. DeGray remained in Rochester until December 22, 1989, when he was recalled to Buffalo. He made his Sabres debut that night at home against the Montreal Canadiens. He appeared again the following night in Quebec as the Sabres took on the Nordiques. On December 26, 1989, he was sent back to Rochester, where he remained for about a month. DeGray was again recalled to Buffalo in late-January, but was returned to Rochester without appearing in a Sabres game. In mid-February, 1990 DeGray was recalled to Buffalo for a more lengthy stint when veteran defenseman Mike Ramsey was injured. He appeared in 4 more games with the Sabres from February 19th to March 2nd, 1990 before he was sent back to Rochester for the remainder of the season. Throughout the course of the season, DeGray saw action in 6 games for the Sabres and was held scoreless in all 6 of his appearances. He finished the season with a -4 plus/minus rating. He saw greater success in his outings with Rochester during the season, scoring 6 goals and 25 assists in 50 games played. He also added 5 goals and 6 assists in the AHL Playoffs, helping the Amerks advance to the Calder Cup Finals.

DeGray returned to Rochester for the 1990-91 season. He scored 9 goals and 25 assists in 64 regular season games played. In the Playoffs, DeGray had 3 goals and 4 assists as the Amerks again lost in the Calder Cup Finals.

At the end of the 1990-91 season, DeGray was a free agent. Unsigned, he sat out the 1991-92 season. He signed with the San Diego Gulls of the International Hockey League, where he played the 1992-93 and 1993-94 seasons. DeGray was the leading scorer among San Diego's defensemen during both of his seasons there.

DeGray started the 1994-95 season as a member of the IHL's Detroit Vipers. 14 games into the season, he was traded to the Cleveland Lumberjacks. DeGray finished the season with Cleveland, scoring 19 goals and 49 assists in 64 games played. Despite missing 17 of the team's 81 games, DeGray was Cleveland's leading scorer for the 1994-95 season.

Over the next 3 seasons, DeGray would play for 4 different IHL teams. He spent time with the Cincinnati Cyclones, Manitoba Moose and Quebec Rafales, before returning for a second stint with the Cleveland Lumberjacks to finish the 1997-98 season. In 1998, the cash-strapped Lumberjacks traded DeGray to the Indianapolis Ice. In return, the Ice would pay the cost of Cleveland's hotel bills for their road games in Indianapolis during the 1998-99 season. DeGray spent the 1998-99 season as a player/assistant coach for the Indianapolis Ice. He appeared in 27 games for the Ice, scoring 3 goals and 11 assists. At the end of the season, DeGray retired from professional hockey to pursue a coaching career.

In September, 1999, DeGray was named head coach of the expansion Rockford Ice Hogs of the United Hockey League. Rockford finished at the bottom of the UHL standing in both the 1999-2000 and 2000-01 seasons. At the end of the 2000-01 season, Dale DeGray was dismissed as coach of the Ice Hogs. He is currently seeking a coaching job elsewhere in professional hockey.